DE2442667A1 - Neue indolderivate, ein verfahren zu ihrer herstellung sowie arzneimittel - Google Patents
Neue indolderivate, ein verfahren zu ihrer herstellung sowie arzneimittelInfo
- Publication number
- DE2442667A1 DE2442667A1 DE2442667A DE2442667A DE2442667A1 DE 2442667 A1 DE2442667 A1 DE 2442667A1 DE 2442667 A DE2442667 A DE 2442667A DE 2442667 A DE2442667 A DE 2442667A DE 2442667 A1 DE2442667 A1 DE 2442667A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- hydrogen atom
- lower alkyl
- phenyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- -1 phenylcarbamyl Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 5
- 125000005544 phthalimido group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 3
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 150000001559 benzoic acids Chemical class 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 5
- 150000002475 indoles Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- DVKBLSXIKZHQAL-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-methylindol-2-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C(N)=C1C1=CC=C(Cl)C=C1 DVKBLSXIKZHQAL-UHFFFAOYSA-N 0.000 description 3
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NWARKHJKTSHGQT-UHFFFAOYSA-N 1-methyl-3-phenylindol-2-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C(N)=C1C1=CC=CC=C1 NWARKHJKTSHGQT-UHFFFAOYSA-N 0.000 description 2
- DCNZSGBRAXNERP-UHFFFAOYSA-N 3-(4-aminophenyl)-1-methylindol-2-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C(N)=C1C1=CC=C(N)C=C1 DCNZSGBRAXNERP-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N 3H-indole Chemical compound C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JMBQPDSQCFZTTI-UHFFFAOYSA-N 1,3,3-trimethylindol-2-imine hydrochloride Chemical compound Cl.C1=CC=C2N(C)C(=N)C(C)(C)C2=C1 JMBQPDSQCFZTTI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MWOODERJGVWYJE-UHFFFAOYSA-N 1-methyl-1-phenylhydrazine Chemical compound CN(N)C1=CC=CC=C1 MWOODERJGVWYJE-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- ZXHHNORIQIOSHG-UHFFFAOYSA-N 1-methyl-3-(4-nitrophenyl)indol-2-amine Chemical compound C12=CC=CC=C2N(C)C(N)=C1C1=CC=C([N+]([O-])=O)C=C1 ZXHHNORIQIOSHG-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical class C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- RYDOQJPDRXMRRP-UHFFFAOYSA-N 2-methylpropan-1-one Chemical compound CC(C)[C]=O RYDOQJPDRXMRRP-UHFFFAOYSA-N 0.000 description 1
- DBINMHDKZFKEMO-UHFFFAOYSA-N 3-(2-chloroethyl)-1-methyl-3H-indol-2-imine hydrochloride Chemical compound Cl.C1=CC=C2N(C)C(=N)C(CCCl)C2=C1 DBINMHDKZFKEMO-UHFFFAOYSA-N 0.000 description 1
- GXODGNJAXAMIBT-UHFFFAOYSA-N 3-(3-chloropropyl)-1-methyl-3H-indol-2-imine hydrochloride Chemical compound Cl.C1=CC=C2N(C)C(=N)C(CCCCl)C2=C1 GXODGNJAXAMIBT-UHFFFAOYSA-N 0.000 description 1
- VGZMVOBWDKASOI-UHFFFAOYSA-N 3-[(3-methoxyphenyl)methyl]-1-methylindol-2-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(CC=2C3=CC=CC=C3N(C)C=2N)=C1 VGZMVOBWDKASOI-UHFFFAOYSA-N 0.000 description 1
- NWODAXPUBLHDFV-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methyl]-1-methylindol-2-amine hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC1=C(N)N(C)C2=CC=CC=C12 NWODAXPUBLHDFV-UHFFFAOYSA-N 0.000 description 1
- FWNNKDOSGRZAPP-UHFFFAOYSA-N 3-phenyl-1h-indol-2-amine Chemical compound NC=1NC2=CC=CC=C2C=1C1=CC=CC=C1 FWNNKDOSGRZAPP-UHFFFAOYSA-N 0.000 description 1
- BSWXXYLZNBZSCV-UHFFFAOYSA-N 4-chloro-N-(1-methyl-3-phenylindol-2-yl)benzamide Chemical compound C=1C=CC=CC=1C=1C2=CC=CC=C2N(C)C=1NC(=O)C1=CC=C(Cl)C=C1 BSWXXYLZNBZSCV-UHFFFAOYSA-N 0.000 description 1
- VLQMALVLALLSDP-UHFFFAOYSA-N 4-chloro-n-(1,3,3-trimethylindol-2-ylidene)benzamide Chemical compound CC1(C)C2=CC=CC=C2N(C)C1=NC(=O)C1=CC=C(Cl)C=C1 VLQMALVLALLSDP-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
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- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
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- XLQXTFNTEGTSFY-UHFFFAOYSA-N N-(1,3,3-trimethylindol-2-ylidene)benzamide Chemical compound CC1(C)C2=CC=CC=C2N(C)C1=NC(=O)C1=CC=CC=C1 XLQXTFNTEGTSFY-UHFFFAOYSA-N 0.000 description 1
- JHRAOJAFYBABQB-UHFFFAOYSA-N N-[4-(2-acetamido-1-methylindol-3-yl)phenyl]acetamide Chemical compound C12=CC=CC=C2N(C)C(NC(=O)C)=C1C1=CC=C(NC(C)=O)C=C1 JHRAOJAFYBABQB-UHFFFAOYSA-N 0.000 description 1
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- 235000021355 Stearic acid Nutrition 0.000 description 1
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- 125000002252 acyl group Chemical group 0.000 description 1
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- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
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- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 230000021235 carbamoylation Effects 0.000 description 1
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- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
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- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
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- 238000004040 coloring Methods 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- RJTZUHVCZIGJMB-UHFFFAOYSA-N hydron;1h-indole;chloride Chemical compound Cl.C1=CC=C2NC=CC2=C1 RJTZUHVCZIGJMB-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- SQTNIHIKXJHLQJ-UHFFFAOYSA-N methyl 2-(2-acetamido-1-methylindol-3-yl)acetate Chemical compound C1=CC=C2C(CC(=O)OC)=C(NC(C)=O)N(C)C2=C1 SQTNIHIKXJHLQJ-UHFFFAOYSA-N 0.000 description 1
- NMBFZVJIMXVTBX-UHFFFAOYSA-N methyl 4-(2-imino-1-methyl-3H-indol-3-yl)butanoate hydrochloride Chemical compound Cl.C1=CC=C2C(CCCC(=O)OC)C(=N)N(C)C2=C1 NMBFZVJIMXVTBX-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- DTMDLXYEHKWXEJ-UHFFFAOYSA-N n'-benzyl-2-methyl-n'-phenylpropanehydrazide Chemical compound C=1C=CC=CC=1N(NC(=O)C(C)C)CC1=CC=CC=C1 DTMDLXYEHKWXEJ-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/36—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4236773A GB1437804A (en) | 1973-09-10 | 1973-09-10 | Indole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2442667A1 true DE2442667A1 (de) | 1975-03-13 |
Family
ID=10424107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2442667A Pending DE2442667A1 (de) | 1973-09-10 | 1974-09-06 | Neue indolderivate, ein verfahren zu ihrer herstellung sowie arzneimittel |
Country Status (20)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3300522A1 (de) * | 1982-01-21 | 1983-07-28 | Sandoz-Patent-GmbH, 7850 Lörrach | 3,3-dialkyl- und 3,3-alkylen-indolinderivate, verfahren zu ihrer herstellung und pharmazeutische praeparate sie enthaltend |
| FR2752575A1 (fr) * | 1996-08-23 | 1998-02-27 | Oreal | Compositions de teinture des fibres keratiniques contenant des derives 2-iminoindoliniques, nouveaux derives, leur procede de synthese, et procede de teinture |
| US5919469A (en) * | 1996-08-23 | 1999-07-06 | L'oreal | Products derived from 2-imino-2,3-dihydro-1H-indoles, processes for their preparation, their use in cosmetics and cosmetic compositions using them |
| US6179883B1 (en) | 1996-08-23 | 2001-01-30 | L'oreal | 2-imino-2,3-dihydro-1H-indole derivatives for dyeing keratin fibers |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4261894A (en) * | 1978-12-04 | 1981-04-14 | Sandoz, Inc. | Process for the preparation of optionally substituted 2,3-indolinediones |
| DE19933857A1 (de) * | 1999-07-23 | 2001-02-01 | Cognis Deutschland Gmbh | Kosmetische Mittel mit Pflanzenextrakten |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL236636A (enrdf_load_stackoverflow) * | 1958-03-03 | |||
| US3320278A (en) * | 1965-06-30 | 1967-05-16 | Merck & Co Inc | Alpha-(2-amino)-3-indolyl lower aliphatic acid derivatives |
| US3869471A (en) * | 1971-07-22 | 1975-03-04 | Velsicol Chemical Corp | Alpha-thiocyanoacetamides |
-
1973
- 1973-09-10 GB GB4236773A patent/GB1437804A/en not_active Expired
-
1974
- 1974-08-14 NO NO742929A patent/NO742929L/no unknown
- 1974-08-15 ZA ZA00745246A patent/ZA745246B/xx unknown
- 1974-08-19 IL IL45499A patent/IL45499A0/xx unknown
- 1974-08-20 IN IN1865/CAL/74A patent/IN140088B/en unknown
- 1974-08-28 NL NL7411445A patent/NL7411445A/xx unknown
- 1974-08-29 FI FI2539/74A patent/FI253974A7/fi unknown
- 1974-09-05 JP JP49102492A patent/JPS5070360A/ja active Pending
- 1974-09-06 DE DE2442667A patent/DE2442667A1/de active Pending
- 1974-09-09 LU LU70876A patent/LU70876A1/xx unknown
- 1974-09-09 US US05/504,205 patent/US3984563A/en not_active Expired - Lifetime
- 1974-09-09 SU SU2057508A patent/SU543345A3/ru active
- 1974-09-09 DD DD180987A patent/DD114074A5/xx unknown
- 1974-09-09 SE SE7411377A patent/SE7411377L/xx not_active Application Discontinuation
- 1974-09-09 DK DK474974A patent/DK474974A/da unknown
- 1974-09-10 FR FR7430635A patent/FR2245353B1/fr not_active Expired
- 1974-09-10 BE BE148378A patent/BE819738A/xx unknown
- 1974-09-10 AU AU73151/74A patent/AU7315174A/en not_active Expired
- 1974-09-10 RO RO7400079946A patent/RO63505A/ro unknown
- 1974-09-10 HU HULE755A patent/HU170294B/hu unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3300522A1 (de) * | 1982-01-21 | 1983-07-28 | Sandoz-Patent-GmbH, 7850 Lörrach | 3,3-dialkyl- und 3,3-alkylen-indolinderivate, verfahren zu ihrer herstellung und pharmazeutische praeparate sie enthaltend |
| FR2752575A1 (fr) * | 1996-08-23 | 1998-02-27 | Oreal | Compositions de teinture des fibres keratiniques contenant des derives 2-iminoindoliniques, nouveaux derives, leur procede de synthese, et procede de teinture |
| US5876465A (en) * | 1996-08-23 | 1999-03-02 | L'oreal | Compositions for dyeing keratin fibres containing 2-iminoindoline derivatives and dyeing process |
| US5919469A (en) * | 1996-08-23 | 1999-07-06 | L'oreal | Products derived from 2-imino-2,3-dihydro-1H-indoles, processes for their preparation, their use in cosmetics and cosmetic compositions using them |
| US6179883B1 (en) | 1996-08-23 | 2001-01-30 | L'oreal | 2-imino-2,3-dihydro-1H-indole derivatives for dyeing keratin fibers |
Also Published As
| Publication number | Publication date |
|---|---|
| SU543345A3 (ru) | 1977-01-15 |
| IN140088B (enrdf_load_stackoverflow) | 1976-09-11 |
| SE7411377L (enrdf_load_stackoverflow) | 1975-03-11 |
| ZA745246B (en) | 1975-08-27 |
| GB1437804A (en) | 1976-06-03 |
| RO63505A (fr) | 1978-10-15 |
| LU70876A1 (enrdf_load_stackoverflow) | 1975-01-02 |
| NL7411445A (nl) | 1975-03-12 |
| DK474974A (enrdf_load_stackoverflow) | 1975-05-12 |
| IL45499A0 (en) | 1974-11-29 |
| FI253974A7 (enrdf_load_stackoverflow) | 1975-03-11 |
| US3984563A (en) | 1976-10-05 |
| BE819738A (fr) | 1974-12-31 |
| JPS5070360A (enrdf_load_stackoverflow) | 1975-06-11 |
| FR2245353B1 (enrdf_load_stackoverflow) | 1978-07-07 |
| FR2245353A1 (enrdf_load_stackoverflow) | 1975-04-25 |
| AU7315174A (en) | 1976-03-18 |
| HU170294B (enrdf_load_stackoverflow) | 1977-05-28 |
| NO742929L (enrdf_load_stackoverflow) | 1975-04-07 |
| DD114074A5 (enrdf_load_stackoverflow) | 1975-07-12 |
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